FIELD OF THE INVENTION
This invention is directed to novel organic compounds and is particularly concerned with a 2,9-dihydro-3H-pyrido-[3,2-c]-s-triazolo[4,3-a][1,5]benzodiazepin-3-ones and a process of production therefor.
The new compounds and the process of production therefor can be illustratively represented as follows: ##SPC4##
Wherein R' and R" are alkyl of 1 to 3 carbon atoms or the group ##EQU8## is pyrrolidino, piperidino, 4-methylpiperazino, or [4-(2-hydroxyethyl)]piperazino; wherein R.sub.2 and R.sub.3 are hydrogen, chloro, bromo, trifluoromethyl, or alkyl defined as above; and wherein R'.sub.4 is alkyl as defined above or ##EQU9## in which n is the integer number 2 or 3 and R', R", or ##EQU10## are defined as above.
The invention therefore has as objective compounds of the formula IV and the pharmacologically acceptable acid addition salts of the compounds of formula IV: ##SPC5##
wherein R.sub.1, R.sub.2, and R.sub.3 are defined as above and R.sub.4 has the significance of hydrogen and R'.sub.4 above.
The more desirable products of this invention are of the formula IVB: ##SPC6##
wherein R'.sub.o, R".sub.o are alkyl of 1 to 3 carbon atoms or together ##EQU11## is 4-methylpiperazino or [4-(2-hydroxyethyl)piperazino]; and wherein R".sub.4 is methyl or ##EQU12## in which n is the integer 2 or 3, and R'.sub.o, R".sub.o, or ##EQU13## are defined as above, and the pharmacologically acceptable acid addition salts thereof.
The most desirable product of this invention are of the formula IVC: ##SPC7##
wherein R'".sub.4 is hydrogen or alkyl of 1 to 3 carbon atoms inclusive, and the pharmacologically acceptable acid addition salts thereof.
The process of this invention comprises: heating a compound of the formula I with phosphorus pentasulfide in an inert organic solvent to obtain the thione II; heating II with an alkyl carbazate to obtain the triazolone III and if desired treating III with an alkylating agent R'.sub.4 X wherein X is chlorine, bromine or iodine and R'.sub.4 is defined as above to obtain the corresponding compound of formula IV.